Fungicide n-cycloalkyl-n-bicyclic-carboxamide derivatives

ABSTRACT

The present invention relates N-cycloalkyl-N-bicyclic-carboxamide, thiocarboxamide or N-substituted carboximidamide derivatives of formula (I) wherein A represents a carbo-linked, 5-membered heterocyclyl group; T represents O, S, N—R a , N—OR a , N—NR a R b  or N—CN; Z 1  represents a C 3 -C 7 -cycloalkyl group; X represents N or a CZ 7  and Z 2 ; Z 3 ; L 1  and L 2  represent various substituents; their process of preparation; preparation intermediate compounds; their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

The present invention relates to N-cycloalkyl-N-bicyclic-carboxamide,thiocarboxamide or N-substituted carboximidamide derivatives, theirprocess of preparation, preparation intermediate compounds, their use asfungicide active agents, particularly in the form of fungicidecompositions, and methods for the control of phytopathogenic fungi,notably of plants, using these compounds or compositions.

In international patent application WO-2007/014290 certainN-substituted-N-bicyclic-carboxamide or thiocarboxamide derivatives aregenerically embraced in a broad disclosure of numerous compounds of thefollowing formula:

wherein W¹ can represent oxygen or sulphur; A can represent NH or CH₂;R¹ can represent a phenyl or heterocyclic ring; G can represent a5-membered heterocyclic ring, more specifically a thiazole ring; W² canrepresent oxygen or sulphur; Q^(a) can represent C₄-C₇-cycloalkyl andQ^(b) can represent a 8-11-membered, partially saturated, bicyclicsystem. However, this document does not specifically disclose norsuggest to select such compounds wherein the nitrogen atom of theN-Q^(a)Q^(b) moiety can be substituted by a cycloalkyl.

It is always of high-interest in agriculture to use novel pesticidecompounds in order to avoid or to control the development of resistantstrains to the active ingredients. It is also of high-interest to usenovel compounds being more active than those already known, with the aimof decreasing the amounts of active compound to be used, whilst at thesame time maintaining effectiveness at least equivalent to the alreadyknown compounds. We have now found a new family of compounds thatpossess the above mentioned effects or advantages.

Accordingly, the present invention providesN-cycloalkyl-N-bicyclic-carboxamide derivatives of formula (I)

wherein

-   -   A represents a carbo-linked, partially saturated or unsaturated,        5-membered heterocyclyl group that can be substituted by up to        four groups R;    -   T represents O, S, N—R^(a), N—OR^(a), N—NR^(a)R^(b) or N—CN;    -   Z¹ represents a non substituted C₃-C₇-cycloalkyl or a C₃-C₇        cycloalkyl substituted by up to 10 atoms or groups that can be        the same or different and that can be selected in the list        consisting of halogen atoms; cyano; C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be        the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl        or carbamoyl;    -   Z² represents a hydrogen atom; a halogen atom; cyano;        C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen        atoms that can be the same or different;    -   L¹ and L², that can be the same or different, represent CZ⁴Z⁵,        NZ⁶, O, S, S(O) or S(O)₂;    -   m represents 1, 2 or 3;    -   X represents CZ⁷ or N;    -   Z³ and Z⁷, that can be the same or different, represent a        hydrogen atom; a halogen atom; nitro; cyano; hydroxyl; thio;        amino; pentafluoro-λ6-thio; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; C₁-C₈-alkoxy;        C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can        be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl;        C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up        to 9 halogen atoms that can be the same or different;        C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen        atoms that can be the same or different; C₂-C₈-alkynyl;        C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can        be the same or different C₂-C₈-alkenyloxy;        C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms that        can be the same or different; C₂-C₈-alkynyloxy;        C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms that        can be the same or different; C₃-C₇-cycloalkyl;        C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl        comprising up to 9 halogen atoms that can be the same or        different; formyl; formyloxy; formylamino; carboxy; carbamoyl;        N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C₁-C₈-alkyl;        C₁-C₈-alkylcarbonyl; to C₁-C₈-halogenoalkylcarbonyl comprising        up to 9 halogen atoms that can be the same or different;        C₁-C₈-alkylcarbamoyl; di-C₁-C₈-alkylcarbamoyl;        N—C₁-C₈-alkyloxycarbamoyl; C₁-C₈-alkoxycarbamoyl;        N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl; C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylaminocarbonyl;        di-C₁-C₈-alkylaminocarbonyl; C₁-C₈-alkylcarbonyloxy;        C₁-C₈-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylcarbonylamino;        C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen        atoms that can be the same or different;        C₁-C₈-alkylaminocarbonyloxy; di-C₁-C₈-alkylaminocarbonyloxy;        C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulphenyl,        C₁-C₈-halogenoalkylsulphenyl comprising up to 9 halogen atoms        that can be the same or different, C₁-C₈-alkylsulphinyl,        C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms        that can be the same or different, C₁-C₈-alkylsulphonyl,        C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms        that can be the same or different, C₁-C₈-alkoxyimino,        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,        (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,        (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a        (benzyloxyimino)-C₁-C₈-alkyl; tri(C₁-C₈-alkyl)silyl;        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; phenyl that can be        substituted by up to 5 groups Q; benzyloxy that can be        substituted by up to 5 groups Q; benzylthio that can be        substituted by up to 5 groups Q; benzylamino that can be        substituted by up to 5 groups Q; naphtyl that can be substituted        by up to 6 groups Q; phenoxy that can be substituted by up to 5        groups Q; phenylamino that can be substituted by up to 5 groups        Q; phenylthio that can be substituted by up to 5 groups Q;        phenylmethylene that can be substituted by up to 5 groups Q;        pyridinyl that can be substituted by up to four groups Q and        pyridinyloxy that can be substituted by up to four groups Q;        phenoxymethylene that can be substituted by up to 5 groups Q;    -   two substituents Z³ or Z⁷ together with the consecutive carbon        atoms to that they are linked can form a 5- or 6-membered,        saturated or non-saturated, carbo- or hetero-cycle, that can be        substituted by up to four groups Q that can be the same or        different;    -   p represents 1, 2, or 3;    -   R, that can be the same or different, represent hydrogen atom;        halogen atom; cyano; nitro; amino; thio; pentafluoro-λ-6-thio;        C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; tri(C₁-C₈-alkyl)silyl;        C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up        to 9 halogen atoms that can be the same or different;        C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen        atoms that can be the same or different; C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9        halogen atoms that can be the same or different;        C₂-C₈-alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl;        C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₁-C₈-alkylsulphinyl;        C₁-C₈-alkyl-sulphonyl; C₁-C₈alkoxyimino;        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; (benzyloxyimino)-C₁-C₈-alkyl;        phenoxy; benzyloxy; benzylthio; benzylamino; naphtyl;        halogenophenoxy comprising up to 9 halogen atoms that can be the        same or different; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylaminocarbonyl;        di-C₁-C₈-alkylaminocarbonyl;    -   R^(a) and R^(b), that can be the same or different, represent a        hydrogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to        9 halogen atoms that can be the same or different;        C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl        comprising up to 9 halogen atoms that can be the same or        different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to        9 halogen atoms that can be the same or different;        C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl;        C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that        can be the same or different; formyl; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphonyl;        C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms        that can be the same or different; phenyl that can be        substituted by up to 5 groups Q; naphthyl that can be        substituted by up to 6 groups Q; phenylmethylene that can be        substituted by up to 5 groups Q; phenylsulphonyl that can be        substituted by up to 5 groups Q;    -   Z⁴ and Z⁵, that can be the same or different, represent a        hydrogen atom; a halogen atoms; cyano; nitro, C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be        the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl        comprising up to 9 halogen atoms that can be the same or        different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl;        C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that        can be the same or different; formyl; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphanyl;        C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphinyl;        C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C_($)-alkylsulphonyl;        C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms        that can be the same or different;    -   Z⁶ represents a hydrogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C_($)-alkenyl;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl        comprising up to 9 halogen atoms that can be the same or        different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl;        C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that        can be the same or different; formyl, C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphonyl;        C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms        that can be the same or different; phenylsulfonyl can be        substituted by up to 5 groups Q; benzyl that can be substituted        by up to 5 groups Q;    -   Q, that can be the same or different, represents a halogen atom;        cyano; nitro; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to        9 halogen atoms that can be the same or different; C₁-C₈-alkoxy;        C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can        be the same or different; C₁-C₈-alkylsulphanyl;        C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms        that can be the same or different; tri(C₁-C₈)alkylsilyl and        tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl;    -   as well as salts, N-oxides, metallic complexes, metalloidic        complexes and optically active or geometric isomers thereof.

Any of the compounds according to the invention can exist as one or morestereoisomers depending on the number of stereogenic units (as definedby the IUPAC rules) in the compound. The invention thus relates equallyto all the stereoisomers, and to the mixtures of all the possiblestereoisomers, in all proportions. The stereoisomers can be separatedaccording to the methods that are known per se by the man ordinaryskilled in the art.

According to the invention, the following generic terms are generallyused with the following meanings:

-   -   halogen means fluorine, chlorine, bromine or iodine;    -   heteroatom can be nitrogen, oxygen or sulphur;    -   halogenated groups, notably haloalkyl, haloalkoxy and cycloalkyl        groups, can comprise up to nine identical or different a halogen        atoms;    -   Any alkyl, alkenyl or alkynyl group can be linear or branched;    -   the term “aryl” means phenyl or naphthyl, optionally substituted        by one to five groups selected in the list consisting of        halogen, [C₁-C₆]-alkyl, [C₁-C₆]-haloalkyl, [C₂-C₆]-alkenyl,        [C₂-C₆]-haloalkenyl, [C₂-C₆]-alkynyl, [C₂-C₆]-haloalkynyl,        [C₁-C₆]-alkoxy, [C₁-C₄]-alkoxy-[C₁-C₄]-alkyl,        [C₁-C₄]-alkoxy-[C₁-C₄]-alkoxy, [C₁-C₆]-haloalkoxy and        [C₁-C₄]-haloalkoxy-[C₁-C₄]-alkyl;    -   In the case of an amino group or the amino moiety of any other        amino-containing group, substituted by two substituents that can        be the same or different, the two substituents together with the        nitrogen atom to that they are linked can form a heterocyclyl        group, preferably a 5- to 7-membered heterocyclyl group, that        can be substituted or that can include other hetero atoms, for        example a morpholino group or piperidinyl.

Preferred compounds of formula (I) according to the invention are thosewherein A is selected in the list consisting of:

-   -   a heterocycle of formula (A¹)

wherein:R¹ to R³ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A²)

wherein:R⁴ to R⁶ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C_(S)-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A³)

wherein:R⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to9 halogen atoms that can be the same or different;R⁸ represents a hydrogen atom or a C₁-C₅-alkyl;

-   -   a heterocycle of formula (A⁴)

wherein:R⁹ to R¹¹ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkyl; amino; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanylC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different;

-   -   a heterocycle of formula (A⁵)

wherein:R¹² to R¹⁴ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A⁶)

wherein:R¹⁵ represents a hydrogen atom; a halogen atom; a cyano; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R¹⁶ and R¹⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkoxycarbonyl; C₁-C₅-alkyl; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R¹⁷ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A⁷)

wherein:R¹⁹ represents a hydrogen atom or a C₁-C₅-alkyl;R²⁰ to R²² that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A⁸)

wherein:R²³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;R²⁴ represents a hydrogen atom or C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁹)

wherein:R²⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;R²⁶ represents a hydrogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen to atoms that can be the same or different;

-   -   a heterocycle of formula (A¹⁰)

wherein:R²⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;R²⁸ represents a hydrogen atom; a halogen atom; amino; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C1-C5-halogenoalkoxy comprising up to 9halogen atoms which can be the same or different; C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can bethe same or different; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;

-   -   a heterocycle of formula (A¹¹)

wherein:R²⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R³⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can bethe same or different; amino; C₁-C₅-alkylamino or di-C₁-C₅-alkylamino;

-   -   a heterocycle of formula (A¹²)

wherein:R³¹ represents a hydrogen atom; a halogen atom or a C₁-C₅-alkyl;R³² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R³³ represents a hydrogen atom; a halogen atom; a nitro; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹³)

wherein:R³⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R³⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano;C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;R³⁶ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A¹⁴)

wherein:R³⁷ and R³⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms which can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; or a C₁-C₅-alkylsulfanyl;R³⁹ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A¹⁵)

wherein:R⁴⁰ and R⁴¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A¹⁶)

wherein:R⁴² and R⁴³ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different or amino;

-   -   a heterocycle of formula (A¹⁷)

wherein:R⁴⁴ and R⁴⁵ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms which can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A¹⁸)

wherein:R⁴⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;R⁴⁶ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different or C₁-C₅-alkylsulphanyl;

-   -   a heterocycle of formula (A¹⁹)

wherein:R⁴⁸ and R⁴⁹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-alkylsulphanyl;

-   -   a heterocycle of formula (A²⁰)

wherein:R⁵⁰ and R⁵¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-alkylsulphanyl;

-   -   a heterocycle of formula (A²¹)

wherein:R⁵² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A²²)

wherein:R⁵³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A²³)

wherein:R⁵⁴ and R⁵⁵ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R⁵⁶ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁴)

wherein:R⁵⁷ and R⁵⁹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R⁵⁸ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁵)

wherein:R⁶⁰ and R⁶¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R⁶² represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁶)

wherein:R⁶³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano;C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; C₁-C₅alkylamino or di(C₁-C₅-alkyl)amino;R⁶⁴ represents a hydrogen atom or C₁-C₅-alkyl;R⁶⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different.

More preferred compounds of formula (I) according are those wherein A isselected in the list consisting of A²; A⁶, A¹⁰ and A¹³.

Even more preferred compounds according to the invention are thosewherein A represents A¹³ wherein R³⁴ represents C₁-C₅-alkylC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R³⁵ represents a hydrogen or a fluorine atom; R³⁶represents methyl.

Other preferred compounds of formula (I) according to the invention arethose wherein T represents O or S.

Other more preferred compounds according to the invention are thosewherein T represents O.

Other preferred compounds of formula (I) according to the invention arethose wherein Z¹ represents cyclopropyl.

Other more preferred compounds according to the invention are thosewherein those wherein Z¹ represents a non-substituted cyclopropyl.

Other preferred compounds of formula (I) according to the invention arethose wherein Z² represents a hydrogen atom.

Other preferred compounds of formula (I) according to the invention arethose wherein L¹ represents CZ⁴Z⁵.

Other preferred compounds of formula (I) according to the invention arethose wherein L² represents CZ⁴Z⁵ and m represents 1 or 2.

Other preferred compounds of formula (I) according to the invention arethose wherein Z³ and Z⁷, that can be the same or different, represent ahydrogen atom; a halogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different.

The above mentioned preferences with regard to the substituents of thecompounds of formula (I) according to the invention can be combined invarious manners, either individually, partially or entirely. Thesecombinations of preferred features thus provide sub-classes of compoundsaccording to the invention. Examples of such sub-classes of preferredcompounds according to the invention can combine:

-   -   preferred features of A with preferred features of one or more        of T, Z¹, Z², L¹, L², m, Z³ and Z⁷;    -   preferred features of T with preferred features of one or more        of A, Z¹, Z², L¹, L², m, Z³ and Z⁷;    -   preferred features of Z¹ with preferred features of one or more        of A, T, Z², L¹, L², m, Z³ and Z⁷;    -   preferred features of Z² with preferred features of one or more        of A, T, Z¹, L¹, L², m, Z³ and Z⁷;    -   preferred features of L¹ with preferred features of one or more        of A, T, Z¹, Z², L², m, Z³ and Z⁷;    -   preferred features of L² with preferred features of one or more        of A, T, Z¹, Z², L², m, Z³ and Z⁷;    -   preferred features of m with preferred features of one or more        of A, T, Z¹, Z², L¹, L², Z³ and Z⁷;    -   preferred features of Z³ with preferred features of one or more        of A, T, Z¹, Z², L¹, L², m, and Z⁷;    -   preferred features of Z⁷ with preferred features of one or more        of A, T, Z¹, Z², L¹, L², m, and Z³.

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of A, T, Z¹,Z², L¹, L², m, Z³ and Z⁷ so as to form most preferred subclasses ofcompounds according to the invention.

The present invention also relates to a process for the preparation ofcompounds of formula (I).

Thus according to a further aspect of the present invention there isprovided a process P1 for the preparation of a compound of formula (I)as herein-defined, as illustrated by the following reaction scheme:

wherein

-   -   T represents O, N—R^(a), N—OR^(a), N—NR^(a)R^(b) or N—CN;    -   Y¹ represents a halogen atom or a hydroxyl;    -   A, Z¹ to Z³, R^(a), R^(b), L¹, L², X, m and p are as        herein-defined

In process P1 according to the invention, step 1 can be performed ifappropriate in the presence of a solvent and if appropriate in thepresence of an acid binder.

N-cycloalkyl-amine derivatives of formula (II) are known or can beprepared by known processes (J. Het. Chem., 1983, p 1031-6; J. Am. Chem.Soc., 2004, p 5192-5201; Synt. Comm. 2003, p 3419-25; Chem. Pharm. Bull,1981, 29(3), 720).

When T represents O, carboxylic acid derivatives of formula (III) areknown or can be prepared by known processes (WO-93/11117; EP-A 0 545099; Nucleosides & Nucleotides, 1987, p 737-759, Bioorg. Med. Chem.,2002, p 2105-2108).

When T represents N—R^(a), N—OR^(a), N—NR^(a)R^(b) or N—CN,N-substituted carboximidoyl chloride derivatives of formula (III) areknown or can be prepared by known processes, for example as described inHouben-Weyl, “Methoden der organischen Chemie” (1985), E5/1, 628-633 andPatai, “The chemistry of amidines and imidates” (1975), 296-301.

Suitable acid binders for carrying out process P1 according to theinvention can be inorganic or organic bases which are customary for suchreactions. Preference is given to using alkaline earth metal or alkalimetal hydroxides, such as sodium hydroxide, calcium hydroxide, potassiumhydroxide or other ammonium hydroxide derivatives; alkali metalcarbonates, such as sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate; alkali metal or alkaline earth metalacetates, such as sodium acetate, potassium acetate, calcium acetate;alkaline earth metal or alkali metal hydrides, such as sodium hydride orpotassium hydride; alkaline earth metal or alkali metal alcoolates, suchas sodium methylate, sodium ethylate, sodium propylate or potassiumt-butylate; and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethyl-aminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diaza-bicycloundecene (DBU) or apolymer-supported acid scavenger (for example as detailed inhttp://www.iris-biotech.de/downloads/scavengers.pdf).

It is also possible to work in the absence of any additional acid binderor to employ an excess of the amine component, so that it simultaneouslyacts as acid binder agent.

Suitable solvents for carrying out process P1 according to the inventioncan be customary inert organic solvents. Preference is given to usingoptionally halogenated aliphatic, alicyclic or aromatic hydrocarbons,such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichlorethane or trichlorethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone, orhexamethylphosphoric triamide; alcohols such as methanol, ethanol,propanol, iso-propanol; esters, such as methyl acetate or ethyl acetate,sulphoxides, such as dimethyl sulphoxide, or sulphones, such assulpholane.

When carrying out process P1 according to the invention, the aminederivative of formula (II) can be employed as its salt, such aschlorhydate or any other convenient salt.

When carrying out process P1 according to the invention, 1 mole or anexcess of the amine derivative of formula (II) and from 1 to 3 moles ofthe acid binder can be employed per mole of the reagent of formula(III).

It is also possible to employ the reaction components in other ratios.Work-up is carried out by known methods.

In general, the reaction mixture is concentrated under reduced pressure.The residue that remains can be freed by known methods, such aschromatography or recrystallization, from any impurities that can stillbe present.

According to a further aspect according to the invention, there isprovided a process P2 for the preparation of a compound of formula (I)wherein T represents S, as herein-defined, as illustrated by thefollowing reaction scheme:

wherein A, Z¹ to Z³, L¹, L², X, m, p and Y are as herein-defined;

Process P2 can be performed in the presence of a thionating agent.

Starting amide derivatives of formula (I) can be prepared according toprocess P1 wherein T represents O.

Suitable thionating agents for carrying out process P2 according to theinvention can be sulphur (S), sulfhydric acid (H₂S), sodium sulfide(Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃),bis(diethylaluminium) sulfide ((AlEt₂)₂S), ammonium sulfide ((NH₄)₂S),phosphorous pentasulfide (P₂S₅), Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) ora polymer-supported thionating reagent such as described in J. Chem.Soc. Perkin 1, (2001), 358. in the presence or not of a catalytic,stoechiometric or more amount of a base such as an inorganic or organicbase. Preference is given to using alkali metal carbonates, such assodium carbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate; heterocyclic aromatic bases, such as pyridine, picoline,lutidine, collidine; and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethyl-aminopyridine or N-methylpiperidine.

Suitable solvents for carrying out process P2 according to the inventioncan be customary inert organic solvents. Preference is given to usingoptionally halogenated aliphatic, alicyclic or aromatic hydrocarbons,such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichlorethane or trichlorethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; nitriles,such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; sulphurous solvents, such as sulpholane or carbondisufide.

When carrying out process P2 according to the invention, 1 mole or anexcess of the sulphur equivalent of the thionating agent and from 1 to 3moles of the base can be employed per mole of the amide reactant (I).

It is also possible to employ the reaction components in other ratios.Work-up is carried out by known methods.

In general, the reaction mixture is concentrated under reduced pressure.The residue that remains can be freed by known methods, such aschromatography or recrystallization, from any impurities that can stillbe present.

When carrying out processes P1 and P2 according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, these processes are carried out at temperatures from 0° C. to160° C., preferably from 10° C. to 120° C. A way to control thetemperature for the processes according to the invention is to usemicro-wave technology.

Processes P1 and P2 according to the invention are generally carried outunder atmospheric pressure. It is also possible to operate underelevated or reduced pressure.

Compounds according to the invention can be prepared according to theabove described to processes. It will nevertheless be understood that,on the basis of his general knowledge and of available publications, theskilled worker will be able to adapt these processes according to thespecifics of each of the compounds according to the invention that isdesired to be synthesized.

Still in a further aspect, the present invention relates to compounds offormula (II) useful as intermediate compounds or materials for theprocess of preparation according to the invention. The present inventionthus provides compounds of formula (II)

wherein Z¹, Z², L¹, L², m, X, Z³ and p are as herein-defined providedthat X represents N when Z⁴ and Z⁵ both represent a hydrogen atom orwhen L² represents NZ⁶ and that compound of formula (II) is not3-(cyclopropylamino)-2,3-dihydro-1,7-dimethyl-1H-indan-4-ol.

In a further aspect, the present invention also relates to a fungicidecomposition comprising an effective and non-phytotoxic amount of anactive compound of formula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention that is sufficient to control ordestroy the fungi present or liable to appear on the crops, and thatdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be controlled, the type of crop, the climatic conditions andthe compounds included in the fungicide composition according to theinvention. This amount can be determined by systematic field trials thatare within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic, organic or inorganic compound with that the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support can be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilisers, water,alcohols, in particular butanol, organic solvents, mineral and plantoils and derivatives thereof. Mixtures of such supports can also beused.

The composition according to the invention can also comprise additionalcomponents. In particular, the composition can further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention can be made, for example, of polyacrylic acidsalts, lignosulphonic acid salts, phenolsulphonic ornaphthalenesulphonic acid salts, polycondensates of ethylene oxide withfatty alcohols or with fatty acids or with fatty amines, substitutedphenols (in particular alkylphenols or arylphenols), salts ofsulphosuccinic acid esters, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols,fatty acid esters of polyols, and derivatives of the above compoundscontaining sulphate, sulphonate and phosphate functions. The presence ofat least one surfactant is generally essential when the active compoundand/or the inert support are water-insoluble and when the vector agentfor the application is water. Preferably, surfactant content can becomprised from 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive that complies with theusual formulation techniques.

In general, the composition according to the invention can contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure), gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ULV) liquid, ultra low volume (ULV) suspension, waterdispersible granules or tablets, water dispersible powder for slurry totreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder. These compositions include not onlycompositions that are ready to be applied to the plant or seed to betreated by means of a suitable device, such as a spraying or dustingdevice, but also concentrated commercial compositions that must bediluted before application to the crop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.The mixtures thus obtained have normally a broadened spectrum ofactivity. The mixtures with other fungicide compounds are particularlyadvantageous.

-   -   Examples of suitable fungicide mixing partners can be selected        in the following lists    -   (1) Inhibitors of the nucleic acid synthesis, for example        benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol,        ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M,        ofurace, oxadixyl and oxolinic acid.    -   (2) Inhibitors of the mitosis and cell division, for example        benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam,        fuberidazole, pencycuron, thiabendazole, thiophanate,        thiophanate-methyl and zoxamide.    -   (3) Inhibitors of the respiration, for example diflumetorim as        Cl-respiration inhibitor; bixafen, boscalid, carboxin, fenfuram,        flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam        (9R-component), isopyrazam (9S-component), mepronil,        oxycarboxin, penthiopyrad, thifluzamide as CII-respiration        inhibitor; amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin,        enestroburin, famoxadone, fenamidone, fluoxastrobin,        kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,        pyraclostrobin, pyribencarb, trifloxystrobin as CIII-respiration        inhibitor.    -   (4) Compounds capable to act as an uncoupler, like for example        binapacryl, dinocap, fluazinam and meptyldinocap.    -   (5) Inhibitors of the ATP production, for example fentin        acetate, fentin chloride, fentin hydroxide, and silthiofam.    -   (6) Inhibitors of the amino acid and/or protein biosynthesis,        for example andoprim, blasticidin-S, cyprodinil, kasugamycin,        kasugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil.    -   (7) Inhibitors of the signal transduction, for example        fenpiclonil, fludioxonil and quinoxyfen.    -   (8) Inhibitors of the lipid and membrane synthesis, for example        biphenyl, chlozolinate, edifenphos, etridiazole, iodocarb,        iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb,        propamocarb hydrochloride, pyrazophos, tolclofos-methyl and        vinclozolin.    -   (9) Inhibitors of the ergosterol biosynthesis, for example        aldimorph, azaconazole, bitertanol, bromuconazole,        cyproconazole, diclobutrazole, difenoconazole, diniconazole,        diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole,        etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin,        fenpropimorph, fluquinconazole, flurprimidol, flusilazole,        flutriafol, furconazole, furconazole-cis, hexaconazole,        imazalil, imazalil sulfate, imibenconazole, ipconazole,        metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole,        paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz,        propiconazole, prothioconazole, pyributicarb, pyrifenox,        quinconazole, simeconazole, spiroxamine, tebuconazole,        terbinafine, tetraconazole, triadimefon, triadimenol,        tridemorph, triflumizole, triforine, triticonazole, uniconazole,        viniconazole and voriconazole.    -   (10) Inhibitors of the cell wall synthesis, for example        benthiavalicarb, dimethomorph, flumorph, iprovalicarb,        mandipropamid, polyoxins, polyoxorim, prothiocarb, validamycin        A, and valiphenal.    -   (11) Inhibitors of the melanine biosynthesis, for example        carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon and        tricyclazole.    -   (12) Compounds capable to induce a host defence, like for        example acibenzolar-S-methyl, probenazole, and tiadinil.    -   (13) Compounds capable to have a multisite action, like for        example bordeaux mixture, captafol, captan, chlorothalonil,        copper naphthenate, copper oxide, copper oxychloride, copper        preparations such as copper hydroxide, copper sulphate,        dichlofluanid, dithianon, dodine, dodine free base, ferbam,        fluorofolpet, folpet, guazatine, guazatine acetate,        iminoctadine, iminoctadine albesilate, iminoctadine triacetate,        mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper,        propamidine, propineb, sulphur and sulphur preparations        including calcium polysulphide, thiram, tolylfluanid, zineb and        ziram.    -   (14) Further compounds like for example        2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, ethyl        (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,        N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,        N-{2-[1,1′-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,        (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,        (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,        2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,        N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,        5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,        (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,        (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,        (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,        1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,        methyl        1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,        N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,        N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,        O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}1H-imidazole-1-carbothioate,        N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide,        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,        5-amino-1,3,4-thiadiazole-2-thiol, propamocarb-fosetyl,        1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl        1H-imidazole-1-carboxylate,        1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,        2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine,        2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-phenylphenol and        salts,        3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,        3,4,5-trichloropyridine-2,6-dicarbonitrile,        3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,        3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,        4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,        quinolin-8-ol, quinolin-8-ol sulfate (2:1) (salt), benthiazole,        bethoxazin, capsimycin, carvone, chinomethionat, chloroneb,        cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet,        debacarb, dichlorophen, diclomezine, dicloran, difenzoquat,        difenzoquat methylsulphate, diphenylamine, ecomate, ferimzone,        flumetover, fluopicolide, fluoroimide, flusulfamide,        fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium,        hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl        (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate,        methyl isothiocyanate, metrafenone,        (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,        mildiomycin, tolnifanide,        N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,        N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,        N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,        N-[1-(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,        N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,        N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,        N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,        natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl,        octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and        salts, phenazine-1-carboxylic acid, phenothrin, phosphorous acid        and its salts, propamocarb fosetylate, propanosine-sodium,        proquinazid, pyrrolnitrine, quintozene, S-prop-2-en-1-yl        5-amino-2-(1-methylethyl)-4-(2-methylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-1-carbothioate,        tecloftalam, tecnazene, triazoxide, trichlamide,        5-chloro-N′-phenyl-N′-prop-2-yn-1-ylthiophene-2-sulfonohydrazide        and zarilamid.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound can also beparticularly advantageous. Examples of suitable bactericide mixingpartners can be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The compounds of formula (I) and the fungicide composition according tothe invention can be used to curatively or preventively control thephytopathogenic fungi of plants or crops. Thus, according to a furtheraspect of the invention, there is provided a method for curatively orpreventively controlling the phytopathogenic fungi of plants or cropscharacterised in that a compound of formula (I) or a fungicidecomposition according to the invention is applied to the seed, the plantor to the fruit of the plant or to the soil wherein the plant is growingor wherein it is desired to grow.

The method of treatment according to the invention can also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theoverground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

Among the plants that may becan be protected by the method according tothe invention, mention may becan be made of cotton; flax; vine; fruit orvegetable crops such as Rosaceae sp. (for instance pip fruit such asapples and pears, but also stone fruit such as apricots, almonds andpeaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp.,Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana treesand plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceaesp. (for instance lemons oranges and grapefruit); Solanaceae sp. (forinstance tomatoes), Liliaceae sp., Asteraceae sp. (for instancelettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp.,Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp.(for instance strawberries); major crops such as Graminae sp. (forinstance maize, lawn or cereals such as wheat, rye, rice, barley andtriticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (forinstance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp.(for instance soybean), Solanaceae sp. (for instance potatoes),Chenopodiaceae sp. (for instance beetroots), Elaeis sp. (for instanceoil palm); horticultural and forest crops; as well as geneticallymodified homologues of these crops.

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention can be made of:

-   -   Powdery Mildew Diseases such as        Blumeria diseases caused for example by Blumeria graminis;        Podosphaera diseases caused for example by Podosphaera        leucotricha;        Sphaerotheca diseases caused for example by Sphaerotheca        fuliginea;        Uncinula diseases caused for example by Uncinula necator;    -   Rust Diseases such as        Gymnosporangium diseases caused for example by Gymnosporangium        sabinae;        Hemileia diseases caused for example by Hemileia vastatrix;        Phakopsora diseases caused for example by Phakopsora pachyrhizi        and Phakopsora meibomiae;        Puccinia diseases caused for example by Puccinia recondite,        Puccinia graminis or Puccinia striiformis;        Uromyces diseases caused for example by Uromyces appendiculatus;    -   Oomycete Diseases such as        Albugo diseases caused for example by Albugo candida;        Bremia diseases caused for example by Bremia lactucae;        Peronospora diseases caused for example by Peronospora pisi and        Peronospora brassicae;        Phytophthora diseases caused for example by Phytophthora        infestans;        Plasmopara diseases caused for example by Plasmopara viticola;        Pseudoperonospora diseases caused for example by        Pseudoperonospora humuli and Pseudoperonospora cubensis;        Pythium diseases caused for example by Pythium ultimum;    -   Leaf spot, Leaf blotch and Leaf Blight Diseases such as        Alternaria diseases caused for example by Alternaria solani;        Cercospora diseases caused for example by Cercospora beticola;        Cladiosporium diseases caused for example by Cladiosporium        cucumerinum;        Cochliobolus diseases caused for example by Cochliobolus sativus        (Conidiaform: Drechslera, Syn: Helminthosporium) or Cochliobolus        miyabeanus;        Colletotrichum diseases caused for example by Colletotrichum        lindemuthianum;        Cycloconium diseases caused for example by Cycloconium        oleaginum;        Diaporthe diseases caused for example by Diaporthe citri;        Elsinoe diseases caused for example by Elsinoe fawcettii;        Gloeosporium diseases caused for example by Gloeosporium        laeticolor;        Glomerella diseases caused for example by Glomerella cingulata;        Guignardia diseases caused for example by Guignardia bidwellii;        Leptosphaeria diseases caused for example by Leptosphaeria        maculans and Leptosphaeria nodorum;        Magnaporthe diseases caused for example by Magnaporthe grisea;        Mycosphaerella diseases caused for example by Mycosphaerella        graminicola, Mycosphaerella arachidicola and Mycosphaerella        fijiensis;        Phaeosphaeria diseases caused for example by Phaeosphaeria        nodorum;        Pyrenophora diseases caused for example by Pyrenophora teres or        Pyrenophora tritici repentis;        Ramularia-diseases caused for example by Ramularia collo-cygni        or Ramularia areola;        Rhynchosporium diseases caused for example by Rhynchosporium        secalis;        Septoria diseases caused for example by Septoria apii and        Septoria lycopersici;        Typhula diseases caused for example by Thyphula incarnate;        Venturia diseases caused for example by Venturia inaequalis;    -   Root-, Sheath and Stem Diseases such as        Corticium diseases caused for example by Corticium graminearum;        Fusarium diseases caused for example by Fusarium oxysporum;        Gaeumannomyces diseases caused for example by Gaeumannomyces        graminis;        Rhizoctonia diseases caused for example by Rhizoctonia solani;        Sarocladium diseases caused for example by Sarocladium oryzae;        Sclerotium diseases caused for example by Sclerotium oryzae;        Tapesia diseases caused for example by Tapesia acuformis;        Thielaviopsis diseases caused for example by Thielaviopsis        basicola;    -   Ear and Panicle Diseases including Maize cob such as        Alternaria diseases caused for example by Alternaria spp.;        Aspergillus diseases caused for example by Aspergillus flavus;        Cladosporium diseases caused for example by Cladiosporium        cladosporioides;        Claviceps diseases caused for example by Claviceps purpurea;        Fusarium diseases caused for example by Fusarium culmorum;        Gibberella diseases caused for example by Gibberella zeae;        Monographella diseases caused for example by Monographella        nivalis;    -   Smut- and Bunt Diseases such as        Sphacelotheca diseases caused for example by Sphacelotheca        reiliana;        Tilletia diseases caused for example by Tilletia caries;        Urocystis diseases caused for example by Urocystis occulta;        Ustilago diseases caused for example by Ustilago nuda;    -   Fruit Rot and Mould Diseases such as        Aspergillus diseases caused for example by Aspergillus flavus;        Botrytis diseases caused for example by Botrytis cinerea;        Penicillium diseases caused for example by Penicillium expansum        and Penicillium purpurogenum;        Rhizopus diseases caused by example by Rhizopus stolonifer        Sclerotinia diseases caused for example by Sclerotinia        sclerotiorum;        Verticillium diseases caused for example by Verticillium        alboatrum;    -   Seed- and Soilborne Decay, Mould, Wilt, Rot and Damping-off        diseases        Alternaria diseases caused for example by Alternaria        brassicicola;        Aphanomyces diseases caused for example by Aphanomyces        euteiches;        Ascochyta diseases caused for example by Ascochyta lentis;        Aspergillus diseases caused for example by Aspergillus flavus;        Cladosporium diseases caused for example by Cladosporium        herbarum;        Cochliobolus diseases caused for example by Cochliobolus        sativus;

(Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium);

Colletotrichum diseases caused for example by Colletotrichum coccodes;Fusarium diseases caused for example by Fusarium culmorum;Gibberella diseases caused for example by Gibberella zeae;Macrophomina diseases caused for example by Macrophomina phaseolina;Microdochium diseases caused for example by Microdochium nivale;Monographella diseases caused for example by Monographella nivalis;Penicillium diseases caused for example by Penicillium expansum;Phoma diseases caused for example by Phoma lingam;Phomopsis diseases caused for example by Phomopsis sojae;Phytophthora diseases caused for example by Phytophthora cactorum;Pyrenophora diseases caused for example by Pyrenophora graminea;Pyricularia diseases caused for example by Pyricularia oryzae;Pythium diseases caused for example by Pythium ultimum;Rhizoctonia diseases caused for example by Rhizoctonia solani;Rhizopus diseases caused for example by Rhizopus oryzae;Sclerotium diseases caused for example by Sclerotium rolfsii;Septoria diseases caused for example by Septoria nodorum;Typhula diseases caused for example by Typhula incarnate;Verticillium diseases caused for example by Verticillium dahliae;

-   -   Canker, Broom and Dieback Diseases such as        Nectria diseases caused for example by Nectria galligena;    -   Blight Diseases such as        Monilinia diseases caused for example by Monilinia laxa;    -   Leaf Blister or Leaf Curl Diseases including deformation of        blooms and fruits such as        Exobasidium diseases caused for example by Exobasidium vexans.        Taphrina diseases caused for example by Taphrina deformans;    -   Decline Diseases of Wooden Plants such as        Esca disease caused for example by Phaeomoniella clamydospora,        Phaeoacremonium aleophilum and Fomitiporia mediterranea;        Ganoderma diseases caused by example by Ganoderma boninense;    -   Diseases of Flowers and Seeds such as        Botrytis diseases caused for example by Botrytis cinerea;    -   Diseases of Tubers such as        Rhizoctonia diseases caused for example by Rhizoctonia solani;        Helminthosporium diseases caused for example by Helminthosporium        solani;    -   Club root diseases such as        Plasmodiophora diseases, cause for example by Plamodiophora        brassicae.    -   Diseases caused by Bacterial Organisms such as        Xanthomanas species for example Xanthomonas campestris pv.        oryzae;        Pseudomonas species for example Pseudomonas syringae pv.        lachrymans;        Erwinia species for example Erwinia amylovora.

The fungicide composition according to the invention can also be usedagainst fungal diseases liable to grow on or inside timber. The term“timber” means all types of species of wood, and all types of working ofthis wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds according to the invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously from 10 to800 g/ha, preferably from 50 to 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given asillustrative examples of the method according to the invention. A personskilled in the art will know how to adapt the application doses, notablyaccording to the nature of the plant or crop to be treated.

The fungicide composition according to the invention can also be used inthe treatment of genetically modified organisms with the compoundsaccording to the invention or the agrochemical compositions according tothe invention. Genetically modified plants are plants into genome ofthat a heterologous gene encoding a protein of interest has been stablyintegrated. The expression “heterologous gene encoding a protein ofinterest” essentially means to genes that give the transformed plant newagronomic properties, or genes for improving the agronomic quality ofthe modified plant.

The compounds or mixtures according to the invention can also be usedfor the preparation of composition useful to curatively or preventivelytreat human or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following table of active or intermediate compoundexamples and the following preparation or efficacy examples.

The following tables illustrates in a non-limiting manner examples ofactive or intermediate compounds according to the invention.

In the following table, M+H (or M−H) means the molecular ion peak, plusor minus 1 a.m.u. (atomic mass unit) respectively, as observed in massspectroscopy and M (Apcl+) means the molecular ion peak as it was foundvia positive atmospheric pressure chemical ionisation in massspectroscopy.

Example Z¹ T A M + H logP 1

cPr O

360 2

cPr O

348 3

cPr O

382 4

cPr S

398 5

cPr O

348 6

cPr O

314 7

cPr O

328 8

cPr O

344 9

cPr O

10

cPr O

370 11

cPr O

382 12

cPr O

328 13

cPr O

342 14

cPr O

15

cPr O

328 16

cPr O

406 17

cPr S

422 18

cPr O

19

cPr O

356 20

cPr O

21

cPr O

356 22

cPr O

386 23

cPr O

24

cPr O

329 25

cPr O

330 26

cPr O

346 27

cPr O

28

cPr O

364 29

cPr O

30

cPr O

406 31

cPr O

404 32

cPr O

502 33

cPr O

470 34

cPr O

405 35

cPr O

434 36

cPr O

378 37

cPr O

362 38

cPr O

400 39

cPr O

368 40

cPr O

382 41

cPr O

410 42

cPr O

382 43

cPr O

436 44

cPr O

402 45

cPr O

402 46

cPr O

460 47

cPr O

414 48

cPr O

398 49

cPr O

384 50

cPr O

400 51

cPr O

382 52

cPr O

396 53

cPr O

410 54

cPr O

420 55

cPr O

362 56

cPr S

378 57

cPr O

312 58

cPr O

326 59

cPr O

354 60

cPr O

326 61

cPr O

380 62

cPr O

346 63

cPr O

346 64

cPr O

404 65

cPr O

358 66

cPr O

342 67

cPr O

328 68

cPr O

344 69

cPr O

344 70

cPr O

326 71

cPr O

340 72

cPr O

354 73

cPr O

378 74

cPr O

366 75

cPr O

400 76

cPr O

366 77

cPr S

78

cPr O

332 79

cPr O

346 80

cPr O

362 81

cPr O

410 82

cPr O

388 83

cPr O

400 84

cPr O

346 85

cPr O

360 86

cPr O

87

cPr O

346 88

cPr O

424 89

cPr O

90

cPr O

374 91

cPr O

92

cPr O

374 93

cPr O

94

cPr O

95

cPr O

347 96

cPr O

348 97

cPr O

364 98

cPr O

436 99

cPr O

382 100

cPr O

101

cPr O

364 102

cPr O

520 103

cPr O

488 104

cPr O

376 105

cPr O

452 106

cPr O

424 107

cPr O

344 108

cPr O

402 109

cPr O

110

cPr O

111

cPr O

112

cPr O

113

cPr O

114

cPr O

115

cPr O

330 116

cPr O

388 117

cPr O

350 118

cPr O

364 119

cPr O

392 120

cPr O

364 121

cPr O

418 122

cPr O

384 123

cPr O

384 124

cPr O

442 125

cPr O

396 126

cPr O

380 127

cPr O

366 128

cPr O

382 129

cPr O

382 130

cPr O

364 131

cPr O

378 132

cPr O

392 133

cPr O

349 134

cPr O

363 135

cPr O

391 136

cPr O

363 137

cPr O

417 138

cPr O

383 139

cPr O

383 140

cPr O

441 141

cPr O

395 142

cPr O

379 143

cPr O

365 144

cPr O

381 145

cPr O

381 146

cPr O

363 147

cPr O

377 148

cPr O

391 149

cPr O

330 150

cPr S

151

cPr O

388 152

cPr O

395 153

cPr O

381 154

cPr O

401 155

cPr O

397 156

cPr O

367 157

cPr O

401 158

cPr O

381 159

cPr O

413 160

cPr O

459 161

cPr O

381 162

cPr O

399 163

cPr O

383 164

cPr O

399

Example Z¹ M + H logP 165

cPr 206 166

cPr 189 167

cPr 1.22 168

cPr 362 169

cPr 294 170

cPr 330 171

cPr 0.81 172

cPr 230 173

cPr 252 174

cPr 1.15 175

cPr 0.32 176

cPr 0.83 177

cPr 0.67 178

cPr 1.26

The following examples illustrate in a non-limiting manner thepreparation and efficacy of the compounds of formula (I) according tothe invention.

PREPARATION EXAMPLEN-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(compound 5) Step 1: preparation of7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine

To a cooled solution of 4.16 ml (60 mmol) of cyclopropylamine and 4.3 ml(75 mmol) of acetic acid, together with 5 g of 3 Å molecular sieves, in80 ml of methanol, are added 5 g (30 mmol) of7-chloro-2,3-dihydro-1H-inden-1-one. The reaction mixture is stirred for4 hrs at reflux. The reaction mixture is then cooled to ambienttemperature and 2.83 g (45 mmol) of sodium cyanoborohydride are slowlyadded. The reaction mixture is further stirred for 2 hrs at reflux. Thesolvent is removed under vacuum and 100 ml of water are then added tothe residue and the pH is adjusted to 10 with sodium hydroxyde. Thewatery layer is extracted three times with dichloromethane (3×50 ml);the combined organic layers are dried over magnesium sulphate andconcentrated in vacuum to yield 5.6 g (80% yield) of7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine as an brown oil(M+1=208).

Step 2: preparation ofN-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

At ambient temperature, a solution of 0.19 g (1.06 mmol) of5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 3 ml oftetrahydrofurane is added dropwise to a solution of 0.20 g (0.96 mmol)of 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine and 0.15 mltriethylamine in 8 ml tetrahydrofurane. The reaction mixture is stirredfor 3 hrs at reflux. The solvent is removed under vacuum and 10 ml ofwater are then added to the residue. The watery layer is extracted threetimes with ethyl acetate (3×20 ml); the combined organic layers aredried over magnesium sulphate and concentrated in vacuum. Columnchromatography (gradient n-heptane/ethyl acetate) yields 0.26 mg (73%yield) ofN-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideas an orange oil (M+1=348).

GENERAL PREPARATION EXAMPLE Thionation of Amide of Formula (I) onChemspeed Apparatus

In a 13 ml Chemspeed vial is weighted 0.27 mmole of phosphorouspentasulfide (P₂S₅). 3 ml of a 0.18 molar solution of the amide (I)(0.54 mmole) in dioxane is added and the mixture is heated at reflux fortwo hours. The temperature is then cooled to 80° C. and 2.5 ml of waterare added. The mixture is heated at 80° C. for one more hour. 2 ml ofwater are then added and the reaction mixture is extracted twice by 4 mlof dichloromethane. The organic phase is deposited on a basic aluminacardridge (2 g) and eluted twice by 8 ml of dichloromethane. Thesolvents are removed and the crude thioamide derivative is analyzed byLCMS and NMR. Insufficiently pure compounds are further purified bypreparative LCMS.

EXAMPLE A In Vivo Test on Pyrenophora teres (Barley Net Blotch)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Barley plants (Express variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Pyrenophora teres spores (12,000 spores per ml).The spores are collected from a 12-day-old culture. The contaminatedbarley plants are incubated for 24 hours at about 20° C. and at 100%relative humidity, and then for 12 days at 80% relative humidity.

Grading is carried out 12 days after the contamination, in comparisonwith the control plants. Under these conditions, good (at least 70%) ortotal protection is observed at a dose of 500 ppm with the followingcompounds: 1, 2, 3, 4, 5, 6, 8, 10, 11, 12, 13, 15, 16, 17, 19, 25, 28,32, 35, 39, 40, 42, 43, 44, 45, 46, 47, 48, 49, 51, 52, 54, 55, 56, 62,63, 64, 65, 69, 73, 74, 75, 76, 78, 79, 80, 81, 82, 83, 84, 85, 87, 90,92, 95, 105, 117, 122, 125, 133, 134, 136, 137, 138, 139 and 141.

EXAMPLE B In Vivo Test on Mycosphaerella graminicola (Wheat Leaf Spot)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove. Plants, used as controls, are treated with an aqueous solutionnot containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Mycosphaerella graminicola spores (500 000 sporesper ml). The spores are collected from a 7-day-old culture. Thecontaminated wheat plants are incubated for 72 hours at 18° C. and at100% relative humidity, and then for 21 to 28 days at 90% relativehumidity. Grading (% of efficacy) is carried out 21 to 28 days after thecontamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 2, 3, 5,6, 7, 8, 10, 15, 16, 19, 22, 24, 30, 31, 34, 35, 39, 40, 41, 42, 43, 44,45, 46, 48, 49, 50, 51, 52, 53, 56, 57, 58, 59, 60, 62, 63, 65, 66, 68,70, 72, 73, 74, 75, 76, 78, 80, 81, 83, 84, 87, 88, 90, 95, 102, 103,105, 106, 107, 115, 116, 117, 118, 119, 121, 122, 123, 130, 131, 132,133, 134, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147,148, 153 and 157.

EXAMPLE C In Vivo Test on Puccinia recondita (Brown Rust)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material. Wheat plants (Scipion variety) sown on 50/50peat soil-pozzolana substrate in starter cups and grown at 12° C., aretreated at the 1-leaf stage (10 cm tall) by spraying with the aqueoussuspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Puccinia recondita spores (100,000 spores perml). The spores are collected from a 10-day-old contaminated wheat andare suspended in water containing 2.5 ml/l of tween 80 10%. Thecontaminated wheat plants are incubated for 24 hours at 20° C. and at100% relative humidity, and then for 10 days at 20° C. and at 70%relative humidity.

Grading is carried out 10 days after the contamination, in comparisonwith the control plants. Under these conditions, good (at least 70%) ortotal protection is observed at a dose of 500 ppm with the followingcompounds: 1, 2, 3, 4, 6, 7, 8, 10, 11, 12, 13, 15, 16, 17, 19, 22, 25,26, 28, 30, 31, 33, 34, 35, 41, 42, 46, 47, 51, 53, 54, 55, 59, 65, 72,73, 75, 84, 85, 87, 88, 90, 92, 96, 99, 101, 104, 106, 108, 116, 141,149 and 151.

EXAMPLE D In Vivo Test on Alternaria brassicae (Leaf Spot of Crucifers)

The active ingredients tested are prepared by potter homogenization in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Radish plants (Pernot variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 18-20° C., are treated at thecotyledon stage by spraying with the active ingredient prepared asdescribed above.

Plants, used as controls, are treated with the mixture ofacetone/tween/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Alternaria brassicae spores (40,000 spores percm³). The spores are collected from a 12 to 13 days-old culture.

The contaminated radish plants are incubated for 6-7 days at about 18°C., under a humid to atmosphere.

Grading is carried out 6 to 7 days after the contamination, incomparison with the control plants. Under these conditions, goodprotection (at least 70%) is observed at a dose of 500 ppm with thefollowing compounds: 2, 3, 4, 5, 7, 11, 12, 13, 17, 19, 25, 28, 31, 39,40, 41, 42, 43, 44, 45, 47, 48, 51, 52, 53, 56, 65, 76, 79, 81, 82, 83,85, 90, 92, 122, 138, 141 and 153.

EXAMPLE E In Vivo Test on Botrytis cinerea (Grey Mould)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material.

Gherkin plants (Vert petit de Paris variety), sown on a 50/50 peatsoil-pozzolana substrate in starter cups and grown at 18-20° C., aretreated at the cotyledon Z11 stage by spraying with the activeingredient prepared as described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material. After 24 hours, the plants arecontaminated by depositing drops of an aqueous suspension of Botrytiscinerea spores (150,000 spores per ml) on upper surface of the leaves.The spores are collected from a 15-day-old culture and are suspended ina nutrient solution composed of:

-   -   20 g/L of gelatin;    -   50 g/L of D-fructose;    -   2 g/L of NH₄NO₃;    -   1 g/L of KH₂PO₄.

The contaminated cucumber plants are settled for 5-7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity.

Grading is carried out 5/7 days after the contamination, in comparisonwith the control plants.

Under these conditions, good (at least 70%) protection is observed at adose of 500 ppm with the following compounds: 1, 2, 5, 6, 12, 15, 16,39, 40, 42, 44, 45, 51, 74, 76, 78, 85, 133 and 138.

EXAMPLE F In Vivo Test on Sphaerotheca fuliginea (Powdery Mildew)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana to substrate and grown at 20° C./23° C., aretreated at the cotyledon Z10 stage by spraying with the aqueoussuspension described above. Plants, used as controls, are treated withan aqueous solution not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Sphaerotheca fuliginea spores (100 000 spores perml). The spores are collected from a contaminated plants. Thecontaminated gherkin plants are incubated at about 20° C./25° C. and at60/70% relative humidity.

Grading (% of efficacy) is carried out 12 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 2, 3, 5,6, 7, 8, 12, 13, 15, 16, 17, 22, 24, 30, 39, 40, 41, 42, 43, 44, 45, 46,48, 49, 50, 51, 52, 54, 56, 57, 59, 62, 64, 65, 66, 67, 70, 71, 72, 73,74, 75, 76, 78, 80, 84, 85, 87, 92, 95, 96, 104, 106, 115, 117, 122,123, 125, 130, 131, 133, 134, 135, 136, 138, 146 and 147.

EXAMPLE G In Vivo Test on Phakopsora pachyrhizi (Soybean Rust)

The active ingredients tested are prepared by homogenization in amixture of acetone/Emulgator PS16. This suspension is then diluted withwater to obtain the desired active material concentration.

Soybean plants (Miyagishirome variety), sown on a horticultural soil inplastic pots and grown at 20° C., are treated at the 1.5-leaf stage (20cm tall) by spraying with the aqueous suspension described above.Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Phakopsora pachyrhizi spores (100,000 spores perml). The spores are collected from contaminated plants. The contaminatedsoybean plants are incubated at about 20° C. and at 80% relativehumidity.

Grading is carried out 11 days after the contamination, in comparisonwith the control plants. Under these conditions, good (at least 70%) ortotal protection is observed at a dose of 250 ppm with the followingcompounds: 1, 12, 13, 17, 19, 31, 90 and 92.

1. A compound of formula (I)

wherein A represents a carbo-linked, partially saturated or unsaturated, 5-membered heterocyclyl group that can be substituted by up to four groups R; T represents O, S, N—R^(a), N—OR^(a), N—NR^(a)R^(b) or N—CN; Z¹ represents a non substituted C₃-C₇-cycloalkyl or a C₃-C₇ cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that can be selected in the list consisting of halogen atoms; cyano; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C_(s)-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl or carbamoyl; Z² represents a hydrogen atom; a halogen atom; cyano; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; L¹ and L², that can be the same or different, represent CZ⁴Z⁵, NZ⁶, O, S, S(O) or S(O)₂; m represents 1, 2 or 3; X represents CZ⁷ or N; Z³ and Z⁷, that can be the same or different, represent a hydrogen atom; a halogen atom; nitro; cyano; hydroxyl; thio; amino; pentafluoro-λ6-thio; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyloxy; C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C₁-C₈-alkyl; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbamoyl; di-C₁-C₈-alkylcarbamoyl; N—C₁-C₈-alkyloxycarbamoyl; C₁-C₈-alkoxycarbamoyl; N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl; C₁-C₈-alkylcarbonyloxy; C₁-C₈-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbonylamino; C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyloxy; di-C₁-C₈-alkylaminocarbonyloxy; C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulphenyl, C₁-C₈-halogenoalkylsulphenyl comprising up to 9 halogen atoms that can be the same or different, C₁-C₈-alkylsulphinyl, C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms that can be the same or different, C₁-C₈-alkylsulphonyl, C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different, C₁-C₈-alkoxyimino, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁-C₈-alkyl; tri(C₁-C₈-alkyl)silyl; tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; phenyl that can be substituted by up to 5 groups Q; benzyloxy that can be substituted by up to 5 groups Q; benzylthio that can be substituted by up to 5 groups Q; benzylamino that can be substituted by up to 5 groups Q; naphtyl that can be substituted by up to 6 groups Q; phenoxy that can be substituted by up to 5 groups Q; phenylamino that can be substituted by up to 5 groups Q; phenylthio that can be substituted by up to 5 groups Q; phenylmethylene that can be substituted by up to 5 groups Q; pyridinyl that can be substituted by up to four groups Q and pyridinyloxy that can be substituted by up to four groups Q; phenoxymethylene that can be substituted by up to 5 groups Q; two substituents Z³ or Z⁷ together with the consecutive carbon atoms to that they are linked can form a 5- or 6-membered, saturated or non-saturated, carbo- or hetero-cycle, that can be substituted by up to four groups Q that can be the same or different; p represents 1, 2, or 3; R, that can be the same or different, represent hydrogen atom; halogen atom; cyano; nitro; amino; thio; pentafluoro-λ-6-thio; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₁-C₈-alkylsulphinyl; C₁-C₈-alkylsulphonyl; C₁-C₈alkoxyimino; (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; (benzyloxyimino)-C₁-C₈-alkyl; phenoxy; benzyloxy; benzylthio; benzylamino; naphtyl; halogenophenoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl; R^(a) and R^(b), that can be the same or different, represent a hydrogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl; C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different; phenyl that can be substituted by up to 5 groups Q; naphthyl that can be substituted by up to 6 groups Q; phenylmethylene that can be substituted by up to 5 groups Q; phenylsulphonyl that can be substituted by up to 5 groups Q; Z⁴ and Z⁵, that can be the same or different, represent a hydrogen atom; a halogen atoms; cyano; nitro, C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphinyl; C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl; C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different; Z⁶ represents a hydrogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl, C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl; C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different; phenylsulfonyl can be substituted by up to 5 groups Q; benzyl that can be substituted by up to 5 groups Q; Q, that can be the same or different, represents a halogen atom; cyano; nitro; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; tri(C₁-C₈)alkylsilyl and tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; as well as salts, N-oxides, metallic complexes, metalloidic complexes and optically active or geometric isomers thereof.
 2. A compound according to claim 1 wherein A is selected in the list consisting of: a heterocycle of formula (A¹)

wherein: R¹ to R³ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A²)

wherein: R⁴ to R⁶ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A³)

wherein: R⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R⁸ represents a hydrogen atom or a C₁-C₅-alkyl; a heterocycle of formula (A⁴)

wherein: R⁹ to R¹¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; amino; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁵)

wherein: R¹² to R¹⁴ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁶)

wherein: R¹⁵ represents a hydrogen atom; a halogen atom; a cyano; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R¹⁶ and R¹⁸ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkoxycarbonyl; C₁-C₅-alkyl; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R¹⁷ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A⁷)

wherein: R¹⁹ represents a hydrogen atom or a C₁-C₅-alkyl; R²⁰ to R²² that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁸)

wherein: R²³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R²⁴ represents a hydrogen atom or C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁹)

wherein: R²⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R²⁶ represents a hydrogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula)(A¹⁰)

wherein: R²⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R²⁸ represents a hydrogen atom; a halogen atom; amino; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C1-C5-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; a heterocycle of formula (A¹¹)

wherein: R²⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R³⁰ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di-C₁-C₅-alkylamino; a heterocycle of formula (A¹²)

wherein: R³¹ represents a hydrogen atom; a halogen atom or a C₁-C₅-alkyl; R³² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R³³ represents a hydrogen atom; a halogen atom; a nitro; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹³)

wherein: R³⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R³⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; R³⁶ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A¹⁴)

wherein: R³⁷ and R³⁸ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; or a C₁-C₅-alkylsulfanyl; R³⁹ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A¹⁵)

wherein: R⁴⁰ and R⁴¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹⁶)

wherein: R⁴² and R⁴³ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or amino; a heterocycle of formula (A¹⁷)

wherein: R⁴⁴ and R⁴⁵ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹⁸)

wherein: R⁴⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R⁴⁶ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-alkylsulphanyl; a heterocycle of formula (A¹⁹)

wherein: R⁴⁸ and R⁴⁹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-alkylsulphanyl; a heterocycle of formula (A²⁰)

wherein: R⁵⁰ and R⁵¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-alkylsulphanyl; a heterocycle of formula (A²¹)

wherein: R⁵² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A²²)

wherein: R⁵³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A²³)

wherein: R⁵⁴ and R⁵⁵ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R⁵⁶ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A²⁴)

wherein: R⁵⁷ and R⁵⁹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R⁵⁸ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A²⁵)

wherein: R⁶⁰ and R⁶¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R⁶² represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A²⁶)

R⁶³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; R⁶⁴ represents a hydrogen atom or C₁-C₅-alkyl; R⁶⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.
 3. A compound according to claim 2 wherein A is selected in the list consisting of A²; A⁶; A¹⁰ and A¹³.
 4. A compound according to claim 3 wherein A represents A¹³, wherein R³⁴ represents C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R³⁵ represents a hydrogen or a fluorine atom and R³⁶ represents methyl.
 5. A compound according claim 1 wherein T represents O or S.
 6. A compound according to claim 5 wherein T represents O.
 7. A compound according to claim 1 wherein Z¹ represents cyclopropyl.
 8. A compound according to claim 1 wherein Z¹ represents a non-substituted cyclopropyl.
 9. A compound according to claim 1 wherein Z² represents a hydrogen atom.
 10. A compound according to claim 1 wherein L¹ represents CZ⁴Z⁵.
 11. A compound according to claim 1 wherein L² represents CZ⁴Z⁵ and m represents 1 or
 2. 12. A compound according to claim 1 wherein Z³ and Z⁷, that can be the same or different, represent a hydrogen atom; a halogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.
 13. A compound of formula (II)

wherein Z¹ represents a non substituted C₃-C₇-cycloalkyl or a C₃-C₇ cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that can be selected in the list consisting of halogen atoms; cyano; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl or carbamoyl; Z² represents a hydrogen atom; a halogen atom; cyano; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; L¹ and L², that can be the same or different, represent CZ⁴Z⁵, NZ⁶, O, S, S(O) or S(O)₂; m represents 1, 2 or 3; X represents CZ⁷ or N; Z³ and Z⁷, that can be the same or different, represent a hydrogen atom; a halogen atom; nitro; cyano; hydroxyl; thio; amino pentafluoro-λ6-thio; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyloxy; C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C₁-C₈-alkyl; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbamoyl; di-C₁-C₈-alkylcarbamoyl; N—C₁-C₈-alkyloxycarbamoyl; C₁-C₈-alkoxycarbamoyl; N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl; C₁-C₈-alkylcarbonyloxy; C₁-C₈-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbonylamino; C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyloxy; di-C₁-C₈-alkylaminocarbonyloxy; C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulphenyl, C₁-C₈-halogenoalkylsulphenyl comprising up to 9 halogen atoms that can be the same or different, C₁-C₈-alkylsulphinyl, C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms that can be the same or different, C₁-C₈-alkylsulphonyl, C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different, C₁-C₈-alkoxyimino, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁-C₈-alkyl; tri(C₁-C₈-alkyl)silyl; tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; phenyl that can be substituted by up to 5 groups Q; benzyloxy that can be substituted by up to 5 groups Q; benzylthio that can be substituted by up to 5 groups Q; benzylamino that can be substituted by up to 5 groups Q; naphtyl that can be substituted by up to 6 groups Q; phenoxy that can be substituted by up to 5 groups Q; phenylamino that can be substituted by up to 5 groups Q; phenylthio that can be substituted by up to 5 groups Q; phenylmethylene that can be substituted by up to 5 groups Q; pyridinyl that can be substituted by up to four groups Q and pyridinyloxy that can be substituted by up to four groups Q; phenoxymethylene that can be substituted by up to 5 group Q; two substituents Z³ or Z⁷ together with the consecutive carbon atoms to that they are linked can form a 5- or 6-membered, saturated or non-saturated, carbo- or hetero-cycle, that can be substituted by up to four groups Q that can be the same or different; and p represents 1, 2, or 3 provided that X represents N when Z⁴ and Z⁵ both represent a hydrogen atom or when L² represents NZ⁶ and that compound of formula (II) is not 3-(cyclopropylamino)-2,3-dihydro-1,7-dimethyl-1H-indan-4-ol.
 14. A fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) according to claim 1 and an agriculturally acceptable support, carrier or filler.
 15. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a compound according to claim 1 is applied to the soil where plants grow or are capable of growing; to the leaves and/or the fruit of plants or to the seeds of plants.
 16. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a composition according to claim 14 is applied to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants. 